(I´m posting remaining answers as replies to the first post)

Q: What might the path to self-healing look like? 

Picking up your cross, standing in the crossroads of the here and now. Putting one foot in front of the other on the path of truth without a name, stretching from one´s own doorstep round the earth and back. To acknowledge the core of your dis-ease in culture, society, in your body, the raw pain of it. Stripped of pompous philosophy. Facing the music and the stark horror of being cast out in an alien desert where you´re forced to lay down, not your life, but your godforsaken crap. Not blinding yourself to the conditions of your bondage, they are in one sense non-negotiable, they will be there. Freedom lies rather in the agency of consciously learning to understand how to relate to your conditioning, from the deepest ground of natural truth. Noone owns the truth, set it free. Like how to nomadic indigenous people the idea of ownership of bits of nature was a ridiculous thing. Getting up and walking in spite of trembling is the thing. Willingly seeing that this point right here is where the need to find healing is greater than one´s laziness or habitual stuckness and fear-driven avoidance patterns. Sharing meat-and-potatoes life hacks and insight. Gratefully making use of the same. Giving comfort to others physically- food, shelter, hugs- but also in the simple example of one´s not quitting on the pilgrimage to Notbullshittown. 

Q: How might the soul avoid/deny/resist their own vulnerability and thus
avoid cultivating the medicine?

Stuffing and numbing the senses with material stimuli to override being starved for true substance.
Going into grandiose guru mode expounding and bible thumping on others to flee your own poverty of spirit. Going on overblown intellectual power trips of gathering a flock of sheep around one to be manipulated  at one´s whim. Going on year-long aimless Jack Kerouac road trips, as a halfbaked phony bid for individuation. Denying your yearning for sensual and spiritual adventure, digging in your heels hard and locking the parking brake tight in consensus stage worldview and hardnosed status quo.  

Q; In what ways might the soul create experiences where they are re-creating
wounding experiences for themself or others?

Wounding might be recreated by overcompensating for being stuck in "the material mud" and the experienced lack of genuine self-trust or self-esteem, and in this acting and speaking recklessly, locked into your own vision and missing to take into consideration the feelings of others and *their* right to their own inner truth. Bumbling ahead eagerly on the path to the top of a mountain- whether defined as exaltedly sensual or pure and spiritual- we see as our own we can forget to give right of way to those people whose different paths may meet and cross ours on that rocky slope.

On the other hand, by staying put excessively in a rut of material or ideological habit, holding back moving along for the sake of existential security and holding feelings at bay of not being good enough, we might betray an authentic calling. Of our own and of those  we interact with and influence in our lives.

Fluctuating between belief systems or life styles in restless seeking, advancing and retreating  alternatively with no real stabilizing center or inner compass to be trusted, could maybe be another way still. 

Q: Wound or sense of being wounded? Feeling of chronically broken?

Being seen as a freak in the tribe for expressing one's authentic views about things long valued as sacrosanct in some way or another. There being noone in the family you can trust and express freely to along lines diverging from the way it´s always been done/what´s always been thought. The imprint of there being no safety in doing this, that being seen for who you really are and this being validated in a balanced way to be trusted, and that this  might endanger securing your basic survival needs. This impacting your basic self-esteem, trust in self and your own truth and as well in life in general.Depression and internalized shame for freely expressing one's natural sensuality and basic sensual needs. Feelings of having to isolate or narrow down one's social scope and to limit who you're talking to and what you're saying and expressing simply to avoid persecution.

What's not accurate here are the emphasis on shame, no one in the family you can trust and express freely relative to how its been done etc. Depression. These speak more to Uranus and Saturn dynamics, not Chiron.

Everything else touches on it.

Self-image of being too thick and slow-witted for advanced learning and study, to advance in one´s studies. Or, too restless to settle for one specific path of study, managing to build towards a goal. i.e. stuck in ever moving and shifting, escaping [?].

Chronic feeling of otherness/unworthiness to do with the body/bodily expressions being seen as inappropriately large (or small)  in different ways according to ordinary standards; big boned, overweight, clumsy, pixie-like etc. Being"too" pretty, mouth "too" wide, "too" touchy-feely, "too"loud, "too" silent etc. 

Chronic indegestion problems[?], stuck in loop of feeding your stomach and all other senses with crap having been sold to you since early childhood sold to you since childhood, for comfort, instead of genuine food for your soul and so chronic experience of emptiness.

One's natural, spontaneous  joyfully expressed, "too"-out-there, spiritual gifts of intuition and need to learn from a wide-ranging number of sources, being made out as wrong and branded as excessive by the priestly lawmakers, law-yers, arbiters of what constitutes the conditions of a sound and balanced life in whatever social tribe/family. Crossing some kind of ideological/theological behavioural  taboo regarding foundational cultural beliefs, and this having to be repressed, narrowed down, flame put out, original voice muted.

The experience of oneself as being stuck in rootless exile since childhood as a stranger in a strange land, having had to escape your country as a political, religious or economical  refugee. Either actually, geographically, and/or in an inwardly sense. Someone experiencing being stuck forever as an "illegal" immigrant, working as an itinerant farm hand not being able to realize their enthusiasm and dreams for education and making a better life for themselves and their family and friends.

The core self esteem stuff, alienation, finding one's path elements resonate here. But a lot of it I'm not sure about. Definitely read my other responses to other students.

The "big" thing is an interesting insight Mathias. There can be an issue of overcompensation or getting involved in teaching/ proposed knowledge that is BEYOND what they actually know.

Q: What might the path to self-healing look like? 

Picking up your cross, standing in the crossroads of the here and now. Putting one foot in front of the other on the path of truth without a name, stretching from one´s own doorstep round the earth and back. To acknowledge the core of your dis-ease in culture, society, in your body, the raw pain of it. Stripped of pompous philosophy. Facing the music and the stark horror of being cast out in an alien desert where you´re forced to lay down, not your life, but your godforsaken crap. Not blinding yourself to the conditions of your bondage, they are in one sense non-negotiable, they will be there. Freedom lies rather in the agency of consciously learning to understand how to relate to your conditioning, from the deepest ground of natural truth. Noone owns the truth, set it free. Like how to nomadic indigenous people the idea of ownership of bits of nature was a ridiculous thing. Getting up and walking in spite of trembling is the thing. Willingly seeing that this point right here is where the need to find healing is greater than one´s laziness or habitual stuckness and fear-driven avoidance patterns. Sharing meat-and-potatoes life hacks and insight. Gratefully making use of the same. Giving comfort to others physically- food, shelter, hugs- but also in the simple example of one´s not quitting on the pilgrimage to Notbullshittown. 

yes to all these things as accurate Taurus 9th house, and I don't feel the Chironic medicinal quality of it too much - the vulnerability, using one's own woundedness as medicine.

Q: How might the soul avoid/deny/resist their own vulnerability and thus
avoid cultivating the medicine?

Stuffing and numbing the senses with material stimuli to override being starved for true substance.
Going into grandiose guru mode expounding and bible thumping on others to flee your own poverty of spirit. Going on overblown intellectual power trips of gathering a flock of sheep around one to be manipulated  at one´s whim. Going on year-long aimless Jack Kerouac road trips, as a halfbaked phony bid for individuation. Denying your yearning for sensual and spiritual adventure, digging in your heels hard and locking the parking brake tight in consensus stage worldview and hardnosed status quo.  

Yes, all can express in that way. Make sure you grasp the heart of Chiron too and what denial/resistance is like here. Read some of the other posts.

Q; In what ways might the soul create experiences where they are re-creating
wounding experiences for themself or others?

Wounding might be recreated by overcompensating for being stuck in "the material mud" and the experienced lack of genuine self-trust or self-esteem, and in this acting and speaking recklessly, locked into your own vision and missing to take into consideration the feelings of others and *their* right to their own inner truth. Bumbling ahead eagerly on the path to the top of a mountain- whether defined as exaltedly sensual or pure and spiritual- we see as our own we can forget to give right of way to those people whose different paths may meet and cross ours on that rocky slope.

On the other hand, by staying put excessively in a rut of material or ideological habit, holding back moving along for the sake of existential security and holding feelings at bay of not being good enough, we might betray an authentic calling. Of our own and of those  we interact with and influence in our lives.

Fluctuating between belief systems or life styles in restless seeking, advancing and retreating  alternatively with no real stabilizing center or inner compass to be trusted, could maybe be another way still. 

Yes to all of this but I sense there is a lacking in the heart of the Chiron experience. You have a general grasp of this signature, and for sure read other posts. I feel that as we practice Chiron and you cultivate more of a lived experienced of it it will all land more. Thank you for your work Mathias.

Thank you for the answers, Ari! I will read  the other answers and try and get a better grasp on Chiron. My own Chiron is exact conjunct Mercury and conjunct moon's south node by a couple of degreesv in Pisces 8th house, so  painfully close to home really.Too much so maybe, I don't know, to get an objective grip on it. In those dark shifting waters. Definitely worth digging into more, for sure

(That's my release point as well, I think. Maybe it's the past life "perpetrator" side of Chiron I'm skirting around. This present life I've made sure to stay mostly inhibited and repressed enough to not be a bad guy in any real way. Even though it, weirdly, may feel like that.)

"...the vulnerability, using one's own woundedness as medicine."

Great, thank you, that's a great, simple definition for my Pisces mind to hang on to.

Thinking about it I realize I am actually [if my Leo AC may say so] in touch with this personally to some degree. And I will try and apply this insight further iin studying other Chiron placements.

To be specific (if possibly long-winding)  this becomes clear to me in my working in healthcare with elderly people. My own Chiron/Mercury wound of chronic ADD opens up for the possibility [on a good day] of a compassionate and kind of natural caring for people whose cognitive faculties, memory, communication skills etc. have become permanently impaired. Really my Chiron stuff has forced me to realize in my bones what may seem as the simple fact that they and I are equals. Which, naturally, goes a long way in establishing a healing connection. Maybe you could say the pain [on a good day] becomes a bridge for mutual healing, even more so than a hindrance.

(Perpetrator shadow side may certainly include a certain over-compensating a**hole wise-ass cleverer-than-thou style, a sometimes too sharp tounge/pen cutting and projecting to quickly on those deemed as foolish, a tiresome need to have the last word etc, etc.)

Mathias, this is a really good example of Chiron and it's living expression, and also expresses your own strong inner connection to it.

Just want to add for those that may not understand this, the "perpetrator shadow side" would apply in this case because of it's placement in the 8th house. Otherwise, on its own Chiron doesn't relate to perpetrator but it could and does relate to how we can cause wounding to others.